Methanesulfonic Acid → HCID 10563488, compound

HRID 1904159Notes

Reaction equation

HRID 1904159 reaction equation
[C:1](/[CH:4]=[CH:5]\[C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([OH:3])=[O:2].NC(N)=S.CS(O)(=O)=O>C(OCC)(=O)C>[C:1](/[CH:4]=[CH:5]/[C:6]([NH:8][C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([OH:3])=[O:2]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 2723790ThioureaHCID 11687575HCID 11687575, compound

Product 1

HCID 10563488HCID 10563488, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
25 °C

Procedure

This compound was isomerized to the fumaryl monoamide using the following procedure. (Z)-N-(3-Carboxy-1-oxo-2-propenyl) -L-phenylalanine (260.0 g.) was mixed with 2.6 1. dry ethyl acetate, 3.80 g. thiourea and 7.19 ml. methanesulfonic acid. The mixture was stirred at reflux temperature for one hour and cooled to 25° C. The crystalline precipitate was collected on a filter, rinsed with 500 ml. ethyl acetate, and dried in air at room temperature to constant weight. The yield of (E)-N-(3-carboxy-1-oxo-2-propenyl)-L-phenylalanine was 226.5 g. (87.1% of theory). The NMR indicated that no Z-isomer was present.

Workup

  1. temperatureat reflux temperature for one hour
  2. customThe crystalline precipitate was collected on a filter
  3. washrinsed with 500 ml
  4. dry with materialethyl acetate, and dried in air at room temperature to constant weight

Sources & evidence

ORD record
ord-93c58704c5ec43238b717194981b258d
Source dataset
uspto-grants-1989_06
Patent number
USH0000645

Reaction notes

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